Ready to take the next step? If you’re planning to propose in Chicago, the city has no shortage of breathtaking locations to make that moment unforgettable. Here are some of the most romantic, photogenic, and iconic spots to pop the question.

I was about 200 feet away in a bush when I took this shot. Andi- the young lady who was proposed too- is a fellow photographer and we know each other. Distance and a good hiding place were KEY here- couldn’t have her connecting the dots!

1. Lurie Garden at Millennium Park

Why It’s Perfect: Nestled in the heart of downtown, Lurie Garden is a serene, blooming oasis with skyline views and vibrant seasonal flowers.
Best Time: Spring and early summer when the garden is in full bloom. Best lighting is when the sun is on west side of skyline! (Think later afternoon to sunset- but anytime will work with a good plan…and photographer!)
Photo Tip: Golden hour lighting reflects beautifully off nearby skyscrapers.
Be aware of Chicago Festivals- they do affect garden hours depending on where the fest is located!

2. Chicago Riverwalk

Why It’s Perfect: With its mix of modern architecture, river views, and hidden alcoves, the Riverwalk offers intimacy and energy.
Best Time: Early morning or late evening for less crowd and soft light.
Photo Tip: Choose the section near the Wabash or Lasalle Bridge for iconic city backdrop shots.

3. North Avenue Beach

Why It’s Perfect: The lakefront skyline view is simply unmatched. A beach proposal at sunrise or sunset is stunning.
Best Time: Sunrise—peaceful, romantic, and nearly empty. Sunset works equally well!
Photo Tip: Propose facing south so the skyline stretches out behind you.

4. The Honeycomb at Lincoln Park

Why It’s Perfect: The architecturally unique Honeycomb (aka the Nature Boardwalk Pavilion) frames the city perfectly.
Best Time: Sunset, with the city aglow behind you.
Photo Tip: Center the couple under the Honeycomb arch for a frame-within-a-frame effect.

5. Alfred Caldwell Lily Pool

Why It’s Perfect: A lesser-known Lincoln Park gem, this spot offers tranquil paths and a private, zen-like atmosphere.
Best Time: Spring or fall for lush colors.
Pro Tip: A permit is required- plan accordingly!

Final Tip:

Plan ahead, bring a photographer (like me!), and let the city become part of your love story. These moments are once-in-a-lifetime- so let’s make them stunning.

Looking for nature-focused locations to propose? Keep an eye out for an upcoming blog on that topic!